Your Twenties are for Experimenting

Some important things are just easier to do while you’re young

Mike Raab
Mike Raab
Sep 18 · 7 min read
Photo by Joshua Earle on Unsplash

Let me first begin by saying that I don’t believe that people are “too old” to do most things in life. Despite what you think the world may expect of you at any given age — if there’s something you’re eager to try, you should absolutely go for it. After all, one of the most common regrets of terminally ill patients is having made major life decisions based on what other people may think about them.

“I wish I’d had the courage to live a life true to myself, not the life others expected of me.” — The Top Five Regrets of the Dying

That said, it seems to me that there are aspects of early-adulthood that can be taken advantage of: namely, free-time, low expectations from others, open-mindedness, and lack of a reputation. Although it may not always feel this way, your twenties are an amazing opportunity to experiment across different aspects of your life with incredibly low-risk. If you take advantage of this time, you can discover things about yourself that may save you lots of anguish down the road: the types of places you like to live in; what you’re both good at and enjoy professionally; and what’s most important to your happiness.

I suspect that many midlife crises are spawned by the realization and admission that a person didn’t deliberately choose their path in life, but instead just did what they thought they were “supposed to do.” Even if they’ve achieved “The American Dream,” which they were assured would make them happy, they realize there were a whole lot of other things that they’d have liked to have tried when they were younger. Perhaps this is the root of the popular phrase “Youth is wasted on the young.”

If this is the case, then the best hedge against future regret is experimenting while you’re young and the stakes are low. Finding the people, places, and profession(s) that make you happy can’t be done by thought experiments, only real experiences. In that spirit, here are the most important things that you can do while you’re young.

Forge Meaningful Relationships

The number one determinant of a deep connection is simply exposure. The more time we spend with someone, the closer we become. When you’re young, you have the ability to spend your free time simply “hanging out” with friends and acquaintances on a regular basis. Perhaps you meetup after work for drinks, share hobbies on the weekend, or have a regularly scheduled dinner or game night.

This repeated exposure on a regular basis is a convenience that you’ll likely see diminish with age. As people start families and have increasing responsibilities at work, their priorities change, and “hanging out” with friends is often de-prioritized. You may be lucky to see a friend or acquaintance twice a month. Take advantage of the free time that you and those around you have at a young age to build meaningful long-lasting relationships, because it only gets more difficult down the road.

Live in Different Places for at least 2 Years

Moving somewhere new can be tough. Of course you’ll likely miss your friends and family back home, which is why it’s important to give yourself time in a new setting to adjust and make new friends. Personally, I think two years is the minimum you should give a potential new hometown to really feel like home. Again — moving to a new place is often easier to do when you’re younger, at least partially because it is easier to make new friends (see above).

Perhaps you’ll find that after living in a couple of new places, you belong back in your hometown after all. Great! This knowledge will spare you potential regret down the road, asking yourself “Would I be happier if I would have moved somewhere else?” On the other hand, you may find that you enjoy the lifestyle better in a new place, or that you have more in common with the people you’ve befriended.

Travel (not vacation)

“Traveling is less uniformly “good” than vacation — some moments will be astoundingly great, and others will be the worst part of your year. But whatever happens may stick around and become part of who you are.” — Tim Urban on WaitButWhy

“Travel is being integrated into a culture that values diverting from the beaten path, talking to locals and exploring an area as one of a kind. Traveling means attempting to blend in and wanting to leave as an altered and more educated person… It’s drinking at neighborhood bars and dives rather than rounding the tourist club circuit. It’s straying from tourist traps and sites and instead, searching for the more elusive history of a country and its people.” — Alessandra S on Elite Daily

The benefits of traveling, at least from my experience, include the shifting of world-perspective, stretching of your empathy muscle, and connecting with people from all over the world. These benefits compound with age — meaning they have a bigger impact if you experience them in your twenties rather than after you retire.

Of course travel isn’t reserved for the young. You may be able to afford cozier accommodations and even visit more exotic places once you’ve saved some money from working for a decade or two. You’ll also likely find that it’s more difficult to achieve the benefits above. One of the great things about exploring in your twenties, especially by yourself, is that it’s an incredibly common thing to do for people around the world. Staying in youth hostels, many of which have age limits, connects you to dozens of likeminded travelers from around the world, which often begins a serendipitous and unforgettable experience. They’re also incredibly cheap.

I’m not saying that it’s impossible to have a transformative travel experience in your forties or beyond, where you meet and connect with other travelers and locals — but it is more difficult.

Try Different Careers

The only way to actually figure out what you’re both good at and enjoy is to try multiple things — much like finding out the type of place you enjoy living in the most. While you’re in school, internships and apprenticeships are a good way to try out careers. But what if you realize in your first real-world job that you actually don’t like or aren’t fit for the career that you’ve chosen? Should you swallow hard and forge on?

Instead, what if we treated our twenties as a career rotational program — trying a handful of different roles at different sized companies in different sectors — and used this experience as a way to definitively measure what’s most important to us in our careers? It’s much easier to switch jobs when you’re young, inexperienced, and not reliant on a large paycheck to pay a mortgage or support a family.

Do it Now or Regret it Later

I’m a personal believer that at the end of our lives, we regret the things we didn’t do more than the things that we did do. Even if you try something and it doesn’t work out as you hoped — you move forward in life with that knowledge instead of a nagging thought in the back of your head asking “What if…?”

If you share this belief, consider treating your youth as the ideal time for experimenting across your life to find the things that matter most to your well being. It won’t always be easy or fun — but it will undoubtedly lead to some self-discovery and empower you to know more about who you are.

The Raabit Hole

Musings on life, entertainment, and technology. Note: opinions expressed do not necessarily represent the views of the author in the future.

Mike Raab

Written by

Mike Raab

I write about media, tech, and life. Currently Director @ The Garage SF, former VC in SF and media strategy professional in LA. For more:

The Raabit Hole

Musings on life, entertainment, and technology. Note: opinions expressed do not necessarily represent the views of the author in the future.

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